Cyrus E. Cheslak

        Associate
        Contact Info
        Cyrus E. Cheslak Cyrus E. Cheslak

        Cyrus is a dedicated, hands-on problem-solver who works closely with clients to help them navigate various employment law matters.

        As a member of Verrill’s Labor and Employment Group, Cyrus assists clients with a variety of employment-related matters, including discrimination and harassment claims, employment litigation, and employee relations. He also supports clients in employment counseling matters, including developing and implementing workplace policies and procedures and advising on compliance with evolving legal obligations.

        Drawing on his strong research and writing skills and background in politics, Cyrus approaches each matter in a thoughtful, methodical, and pragmatic way, tailoring his work to align with each client’s operations and goals.

        During law school, Cyrus was a student attorney for the Cumberland County District Attorney’s Office and Cumberland Legal Aid Clinic, and a judicial expert to the Honorable Kermit V. Lipez of the United States Court of Appeals for the First Circuit. He also served as a teaching assistant for the Legal Research & Writing Program and tutored first-year law students, served as Head Case Note & Comment Editor of the Maine Law Review, and competed on Maine Law’s Trial Competition and Moot Court Teams. After graduating magna cum laude from the University of Maine School of Law, Cyrus clerked for The Honorable Thomas E. Humphrey of the Maine Supreme Judicial Court.

        Prior to law school, Cyrus was an aide to United States Senator Susan M. Collins in Washington D.C., where he worked on a variety of legislative matters including health care, agriculture, and nutrition policy, and managed the office’s administrative operations. Cyrus maintains a strong interest in the public policy space.

        Cyrus now lives in Portland with his family and two dogs, where he enjoys hosting backyard barbeques, visiting Maine’s famed breweries, and hiking and exploring Maine’s natural beauty with his kids.

        Services/Industries

        Education

        • University of Maine School of Law (J.D., magna cum laude)
          • Head Case Note & Comment Editor – Maine Law Review
        • Franklin & Marshall College (B.A.)

        Public Service

        • Maine State Bar Association Leadership Academy

        Bar Admissions

        • Maine
        • Massachusetts

        Court and Other Admissions

        • U.S. District Court for the District of Maine

        Memberships

        • Maine State Bar Association
        • Tri-State Defense Lawyers Association
        • Cumberland Bar Association

        Honors

        • Best Brief, Craven Moot Court Competition
        • Faculty Significant Achievement Award
        • Named to New England Super Lawyers Rising Stars list under Civil Litigation: Defense

        Learn more about the third-party ratings, rankings, and selection processes used for inclusion.

        Clerkships

        • Maine Supreme Judicial Court, Justice Humphrey
        Events
        When: June 24, 2026 at 11:00am - 12:00pm
        Location: Webinar

        Firm Highlights

        Press Releases

        Verrill Recognized by U.S. News as One of the Best Law Firms to Work for in 2026

        BOSTON, Mass., BANGOR and PORTLAND, Maine, GREENWICH and WESTPORT, Conn., – Verrill has been featured on U.S. News’ 2026 Best Companies to Work...
        Blog

        SECURE 2.0 Roth Catch-Up Rules and the 403(b) 15-Year Catch-Up: What Tax-Exempt Employers Need to Know

        Tax-exempt employers whose 403(b) plans offer catch-up contributions for participants age 50 and above should be well on their way to compliance with...
        Media Mentions

        Robert Keach Quoted in Law360 on SIMAD Summer Camp Bankruptcy Sale

        Verrill attorney Robert Keach was recently quoted in a Law360 article examining the Chapter 11 bankruptcy proceedings involving SIMAD Holdings and...
        Media Mentions

        Chris Tsouros Featured in Law360’s Coverage of Sports Real Estate Deals

        Verrill Partner Chris Tsouros was recently recognized in a Law360 article highlighting law firms involved in significant sports real estate projects...
        Blog

        What Maine’s New Employer Surveillance Law Means for Maine Employers

        Maine employers who monitor their workforce, whether through productivity software, GPS, call recording, or cameras, have a new compliance obligation...
        Blog

        Run Don’t Walk: The Implication of “While Supplies Last” Prize Promotions

        This month a big-chain grocery store has been offering daily mystery boxes during specific timed drops on a first-come, first-served basis, to users...
        Blog

        Maine’s Noncompete Statute is Reshaped for Health Care Workers: What You Need to Know

        Employers of individuals who are licensed under state law to perform, or provide, health care services in the State of Maine should be prepared for...
        Media Mentions

        Steven Davis Featured in the Environmental Business Journal

        Steven Davis, President of Verrill Strategic Consulting, was recently interviewed and featured in the Environmental Business Journal, Volume 39...
        Blog

        What is a Bonus for Purposes of ERISA?

        An ongoing dispute about a Department of Labor advisory opinion published last September raises a basic but unanswered question under the ERISA: What...
        Media Mentions

        Verrill Recognized by WMTW for Partnership Supporting Hunger Relief in Maine

        Verrill was recently featured in coverage by WMTW News 8 for its role in a collaborative effort to combat food insecurity across southern...
        Press Releases

        33 Verrill Attorneys, Across Four Offices, Recognized in the 2026 Chambers USA Guide

        BOSTON, Massachusetts, PORTLAND, Maine, WESTPORT, Connecticut, and WASHINGTON, D.C. – Verrill has been recognized as a Leading Firm in 14...
        Blog

        Will the Knicks Beat the Spurs? (Are Prediction Market Event Contracts Gambling?)

        For those of you who like to keep score, currently 18 states are engaged in litigation over prediction markets, such as Kalshi and Polymarket,...